BIOLUMINESCENCE&

CHEMILUMINESCENCEProgress & Current Applications

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editors

Philip E. StanleyCambridge Research & Technology Transfer Ltd., England

Larry J. KrickaDepartment of Pathology & Laboratory Medicine

University of Pennsylvania School of Medicine, USA

World ScientificNew Jersey London • Singapore • Hong Kong

CONTENTS

Preface v

IN MEMORIAM: THE GORDON STEWART MEMORIAL LECTUREContributions Of Light-Emitting Organisms To Cellular AndBiomedical Imaging 3

Szalay AA

PART 1. BIOLUMINESCENCE

Testing of the computer models predictive power for the Lingulodinium{Gonyaulax) polyedra bioluminescence circadian system(Preliminary Report) 15

Berden Zrimec M and Zrimec A

The structural determinants of bioluminescence colors in railroadworm and other pH-insensitive luciferases 19

Viviani VR, UchidaA, Viviani W and Ohmiya Y

PART 2. BEETLE BIOLUMINESCENCE

Mechanism of firefly flash control: nitric oxide inhibition of oxygenconsumption in lantern mitochondria is reversed by light 25

Aprille JR, Lagace CJ, Lewis SM, Michel T, Modica-Napolitano JS,Trimmer BA and Zayas RM

Origins of bioluminescence in beetles: A phylogenetic perspective 29Day JC, White PJ, Squirrell DJ and Bailey MJ

Structural study of Photinus pyralis firefly luciferase using fluorescence 33Gandelman OA, Tisi LC, Law EG, Lowe CR and Murray JAH

Altering the surface hydrophobicity of firefly luciferase 37Law GH, Gandelman OA, Tisi LC, Lowe CR and Murray JAH

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Interaction of firefly luciferase Luciola mingrelica with dimethyloxyluciferin 41Leontieva OV, Vlasova TN, Ugarova NN and Weiss D

Catalytic properties and bioluminescence spectra of recombinant fireflyluciferase Luciola mingrelica with point mutations out of the enzymeactive site 45

Maloshenok LG and Ugarova NN

Red shifts in firefly bioluminescence spectra 49Nemtseva EV, Kudryasheva NS, Leontieva OV and Ugarova NN

On the evolution and synthesis of beetle luciferin: clues from thesimilarity of bacterial siderophores to beetle luciferin 53

Tisi LC, Law GH, Lowik DWPM and Murray JAH

The basis of the bathochromic shift in the luciferase from Photinus pyralis 57Tisi LC, Law GH, Gandelman O, Lowe CR and Murray JAH

Protein structure and bioluminescent spectra for firefly bioluminescence 61Ugarova NN and Brovko LYu

Optical properties of firefly oxyluciferin: the light emitter in fireflyChemi- and bioluminescence 67

Wada N and Sameshima K

PART 3. MARINE BACTERIA BIOLUMINESCENCE

Luminescence-stimulated DNA repair in various bacterial strains 73Czyz A, Plata K, Zielke R and Wegrzyn G

Evaluation of the affinity of bacterial luciferases for immobilization onhydrophobic supports 77

Hosseinkhani S, Szittner R, Nemat-Gorgani M and Meighen E

Relationship between spectral distribution of Vibrio fischeri strain Ylbioluminescence and intracellular level of its fluorescent proteins 81

Karatani H, Chiba T and Hirayama S

Contents x v

Construction and characterization of a bioluminescentStreptococcus pyogenes 85

Lamberton GR, Pereau MJ, Illes K, Kelly IL, ChrislerJ, Childers BJ,Oberg KC and Szalay AA

Binding of flavin and aldehyde to the active site of bacterial luciferase 89Lin LY-C, Szittner R and Meighen EA

Effect of S AM-related structural and regulatory proteins on luminescence inVibrio harveyi 93

Miyamoto C, Lin LY, Huang S-Yand Meighen EA

Common features of the quorum sensing systems in Vibrio species 97Miyamoto C, SkourisN, Hosseinkhani S, Lin LY and Meighen EA

Mechanism of influence of quinones on bioluminescent enzyme systemNAD(P)H:FMN-oxidoreductase-luciferase 101

Vetrova EVand Kudryasheva NS

PART 4. COELENTERATE BIOLUMINESCENCE

Apoobelin biotinylated in vivo: Overproduction in Escherichia coli cells 107Markova SV, Stepanyuk GA, Frank LA and Vysotski ES

Imaging the fluorescence lifetime of green fluorescent protein reports on therefractive index 111

Suhling K, SiegelJ, Phillips D, Sandrine L-F, Webb SED,French PMW and Davis DM

Three-phase partitioning (TPP): A rapid and preparative purificationtool for GFP 115

Thomson CM and Ward WW

Phototransformation of the wild-type Aequorea victoria greenfluorescent protein with UV- and visible light leads todecarboxylation of glutamate 222 119

van ThorJJ, Gensch T, Hellingwerf KJ and Johnson LN

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Fluorescent proteins: Who's got 'em and why? 123WardWW

PART 5. CHEMILUMINESCENCE

Formation of singlet oxygen during the decomposition ofdimethyldioxirane catalyzed by anionic nucleophiles 129

Adam W, Kiefer W, Schlucker S, Saha-Moller C, Kazakov DV,Kazakov VP and Latypova RR

Iron-mediated hydroxylation of phthalic hydrazide 133Arnhold J and Geyer J

Chemiluminescent excitation and the photodynamic effect onbacterial strains 137

Bancifovd M and Medkovd J

A study of chemiluminescence from reactions of peroxyoxalate esters,qhydrogen peroxide and 7-amino-4-trifluoromethylcoumarin 141

Chaichi MJ and Shamsipour M

Stabilized chemiluminescent 1,2-dioxetanes 145Giri BP, Dagli DJ, Toben NE, Giri KW, PrzybyszAJ, Toben VP,Singh P and Toben HR

Coelenterazine derivatives for improved solution stability 149Hawkins EM, O'GradyM, KlaubertD, Scurria M, Good T,Straford C, Flemming R, Simpson D and Wood KV

Non-trivial energy transfer processes in micellar solutions ofphthalhydrazide and selected dyes 153

Hrbac J, Lasovsky J and Sichertova D

Electrogenerated chemiluminescence behavior of a Ru(bpy)32+ system on

a paraffin-impregnated graphite electrode 157LiF, Cui Hand Lin XQ

Contents xvii

The role of ortho- and para-semiquinones in the chemiluminescence andantioxidizing activity of humus substances 161

Polewski K, Slawinska D and Slawinski J

Modulation of the enhanced chemiluminescence with anti-peroxidasespecific antibodies 165

Rubtsova MYU, Ignatenko OV, Cherednikova TV and Egorov AM

Investigations on the thermal stability of 1,2-dioxetanes and thekinetics of decomposition measured via Differential Scanning Calorimetry 169

Weiss D, Flammersheim HJ and Baader WJ

PART 6. LUMINESCENCE IN EDUCATION

Bioluminescence as an educational tool 175Gitelson Jl and Kratasyuk VA

The Da Vinci-Darwin-Linnaeus Initiative: Toward a new Renaissance forscience in Europe 183

Pazzagli M, Gelmini S, Pinzani P, Bergsten P, Nosova Oand Campbell AK

PART 7. INSTRUMENTATION & DEVICES

Photodetector calibration method for reporting bioluminescencemeasurements in standardized units 189

Bartholomeusz DA and Andrade JD

Development of a sensitive instrument for bioluminescence resonanceenergy transfer (BRET) applications 193

Berthold F, Johnson CH, Kanauchi A, Heding A, Peukert M,Hennecke M and Hutter B

A new AUV platform for studying near shore bioluminescence structure 197Blackwell S, Case J, Glenn S, Kohut J, Moline M, Purcell M,Schofield O and Vonalt C

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Electron multiplying CCD technology for ultrasensitive detection ofchemiluminescence 201

Coates CG, Denvir DJ and Conroy EK

Application of a polynomial least squares filter for the reduction ofnoise in the determination of ATP by a batch photometer 205

Mecozzi M, Amici M and Acquistucci R

A novel microtiter plate format for single-well simultaneous multi-analytechemiluminescent detection: application for the development ofa PCR assay for typing human papillomavirus DNA 209

Roda A, Mirasoli M, Venturoli S, Baraldini M and Musiani M

Critical considerations in the use of photomultipliers in chemi- andbioluminescence applications 213

Wright AG

Chemiluminescence detection for field-flow fractionation 217Zattoni A, Roda B, Guardigli M, Melucci D, Reschiglian Pand Roda A

PART 8. ANTIOXIDANTS, REACTIVE OXYGEN SPECIES &PHAGOCYTOSIS

Molecular oxygen (O2): Reactivity and luminescence 223Allen RC

Pholasin® luminescence of polymorphonuclear leukocytes 233Arnhold J, Reichl S, Petkovic Mand Vocks A

Determination of reactive oxygen species during the photodynamiceffect based on chemiluminescence of Cypridina luciferin analogues 237

Bancirovd M

Peripheral and local antioxidant defence in periodontal disease andhealth by enhanced chemiluminescence 241

Brock GR, Matthews JB, Harding CR and Chappie ILC

Contents ^ix

Blood leukocyte luminescence bioassay: a eukaryotic approach tostudying the effects of toxic chemicals on metabolism 245

Cairo JM and Allen RC

Whole blood chemiluminescence in travertine workers 249De Sole P, Fresu R, Rossi C, Gozzo ML, Gammarota E, Spadaro S,Serra M and Mormile F

Evaluation of reactive oxygen species production in Kupffer cells bychemiluminescence 253

Guardigli M, Roda A, Aldini R, Marangoni A and Cevenini R

The ABEL® peroxynitrite antioxidant test with Pholasin® measures theantioxidant capacity of plasma to protect against peroxyl radical attack 257

Knight J, Ganderton M, Hothersall J, Zitouni K and Nourooz-Zadeh J

Chemiluminescence as a tool to assess hyperglycemia-induced systemicoxidative stress in different insulin-resistant states 261

Kopprasch S, Pietzsch J, Kuhlisch E and Graessler J

Luminescence studies of blood phagocyte oxygenation activities inpatients with antiphospholipid syndrome 265

Kopprasch S, Roch B, Pietzsch J, Kuhlisch Eand Graessler J

Chemiluminescence of isolated human leukocytes induced byStreptococcus mutans is generated extracellularly in the absence ofphagocytosis 269

LojekA, Ciz M, Kubala L, Nuutila J and Lilius E-M

Determination of active oxygen species from heat-browned foodmaterials using a highly sensitive chemiluminescence detector 273

Matsuya H, Suzuki N and Yoda B

Chemiluminescence kinetics of blood and milk neutrophils duringphysiological and pathological conditions of the bovine mammary gland 277

Mehrzad J, Meyer E and Burvenich C

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Luminescence as differentiation marker in human leukemia cell line HL-60 281Nocca G, Scatena R, Bottoni P, Ceccarelli L, Giardina Band De Sole P

Effect of the histaminergic system on human polymorphonuclearleukocyte aggregation and respiratory burst in vitro 285

NosdlR, Drdbikovd K, Jancinova V, Ciz M and Lojek A

Lysophosphatidylcholine and phospholipase A2 affect the oxidativeactivity of human polymorphonuclear leukocytes 289

PetkovicM, MullerJ, Schiller J, Arnold K and Arnhold J

Respiratory burst response of human neutrophils to exogenously addedlong chain phosphatidic acids 293

Petkovic M, Zschbrnig O, Vocks A, Midler M, Schiller J,Arnold K and Arnhold J

Antioxidative activities of some dietary fibers against superoxide 297Suzuki N, Nagai T, Hatate H, Mizumoto I, Yoda B, Itami T,Takahashi Y, Nomoto T, Kanamori N and Kozawa A

Antioxidant activity in extracts from Pleurochaete squarrosa (Bryophyta)stressed by heavy metals, heat shock and salinity 301

Vuotto ML, De Sole P, Castaldo Cobianchi R, Sorbo S, Sepe J, FaiellaMR, Miranda R, Ricciardi L, Spatuzzi D, De Prisco R and Basile A

Antioxidant capacity of various samples measured with achemiluminescence system based on GZ-11 305

Zomer G, Hamzink MRJ and Bijlsma L

Development of an assay for antioxidant activity using acridan ester GZ-11 309Zomer G, Hoogerbrugge R, Hamzink MRJ and Bijlsma L

PART 9. APPLICATIONS OF LUMINESCENCE

The use of luminol chemiluminescence for determining the post morteminterval of skeletal remains 315

Creamer JI, Quickenden Tl and Buck AM

Contents xxi

Persistent increase of H2O2 in expired breath condensate of smokers 319De Sole P, Zappacosta B, Persichilli S, Minucci A, Mormile F,Russo A, Sposi A and Vuotto ML

Bioluminescent bioassays based on luminous bacteria marker system 323Kuznetsov AM, Rodicheva EK, Medvedeva SE and Gitelson JI

Comparison of bioluminescence-based methods for detecting bacterialquorum sensing molecules in Pseudomonas fluorescens 327

McPhee JD1 and Griffiths MW

Development and characterization of a fluorescent whole-cell biosensor forL-arabinose with internal response correction using two GFP mutants 331

Mirasoli M, Feliciano-Cardona JS, Michelini E, Roda Aand Daunert S

Determination of hydrogen peroxide by micro-flow injection — horseradishperoxidase catalyzed "imidazole chemiluminescence" 335Nozaki O and Kawamoto H

Chemiluminescence, real time imaging of microparticles separation byfield-flow fractionation: a useful tool for probing retention mechanism atultra-low detection limits 339

Roda B, Zattoni A, Guardigli M, Melucci D, Reschiglian Pand Roda A

Analytical applications of a new aqueous peroxyoxalate chemiluminescencereagent. Comparison with the typical TCPO reaction in organic solvent 343Salerno D and Daban J-R

Application of chemiluminescence in wood science 347Slawinska D and Polewski K

PART 10. PATHOGEN DETECTION

Rapid foodborne pathogen detection 353Bown KJ, Archard JA, CorbittAJ, Leslie RL Murphy MJand Squirrell DJ

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Visualization of intracellular bacterial infection in tumor cell lines 357Greer LF, Wang-Pruski G, Goebel W and Szalay AA

Rapid detection of MRS A from clinical samples using magneticseparation and AK bioluminescence 361

Leslie RL Squirrell DJ, White PJ and Green JCD

A novel dual reporter assay for studying intracellular bacterialpathogens 365

Qazi SNA, Rees CED, Williams P and Hill PJ

ATP screening of bacteria/spores in environmental samples byFirst Responders 369

Trudil DP, Tartal J and Trudil C

PART 11. ECOLOGICAL, ENVIRONMENTAL & FOOD TESTING

Evaluation of preservatives for value added food products usingbioluminescence 375

Applegate BM Jr, Bright NG, Carroll RJ, Mauer LJ andApplegate BM Sr

Seasonal variation in bioluminescence in the Porcupine Seabight, NEAtlantic Ocean to 4800m depth 379

Battle EJV, Priede IG, Collins MA and Bagley PM

Ecotoxicological screening of Ljubljana surface waters withbioluminescent bacteria Vibrio fischeri (Microtox®) 383

Berden Zrimec M and Zrimec A

Activation of warning luminescence by larval firefly setae 387Carlson AD and Shah S

A possible retinal longwave detecting system in a myctophid fish withoutfar-red bioluminescence: Evidence for a sensory arms-race in the deep-sea 391

Douglas RH, Bowmaker JK and Mullineaux CW

Contents xxjjj

Simple and rapid bioluminescent detection for allele specific PCR ofE. coli O 157: H7 395

Imamura O, Arakawa H and Maeda M

Use of bacterial bioluminescent bioassay by schoolchildren forecology monitoring and relations with human health 399

Kudryashev MA, Gavrichkova OV, Kudryasheva NS, Kratasyuk VAand Kuznetsov AM

Chemiluminescent dipstick immunoassay for multiresidue analysis ofpesticides in water 403

Rubtsova MYU, Samsonova JV, Ezhov AA and Egorov AM

The development of a whole cell biochip for toxicant detection 407Waldie FL Binnie TD and Christofi N

PART 12. IMMUNOASSAYS

Immunodetection of proteins within polyacrylamide gels 413Desai S, Dworecki B and Cichon E

Development of allergology test in microplate immunoassay formatbased on chemiluminescence 417

Pazzagli M, Pinzani P, Salvadori B, Salti S, Passeri L and Manzoni A

Applications of Lumigen PS-1 chemiluminescent substrate to microplateformat immunoassay using horseradish peroxidase as label: a comparison withthe colorimetric end-point using TSH as the analyte 421

Pazzagli M, Pinzani P, Salvadori B, Salti S, Zotti MG and Manzoni A

Combined Hepatitis C virus antigen and antibody assay on an automatedchemiluminescent analyzer to shorten seroconversion window 425

Shah DO, Jiang L, Cheng K, MuerhoffS, Gutierrez RA , Kyrk R,Chang C-D, Patel J, Stewart JL and Dawson G

An enhanced chemiluminescent immunoassay to detect insulin 431YangX

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Use of bioluminescence for the evaluation of affinity constants for bacterialcell-antibody interactions 435

Young D, Griffiths MW and Brovko L

PART 13. ENZYME, SUBSTRATE, INHIBITOR & CO-FACTOR ASSAYS

Lactate assay based on bacterial bioluminescence: Enhancement, dry reagentdevelopment, and miniaturization 441

Davies RH, Corry JW and Andrade JD

Enzyme kinetics model of the bacterial luciferase reactions for biosensorapplication 445

Feng Y, Davies RH and Andrade JD

Single molecule detection of alkaline phosphatase enzyme 449Giri BP, Toben HR, Dagli DJ, Lamkin MS and Shinefeld LA

Development of simultaneous bioluminescent assay of acetate kinase andpyruvate phosphate dikinase using firefly luciferase-luciferin reaction 453

ho K, Nakagawa K, Murakami S, Arakawa H and Maeda M

A novel bioluminescent cycling assay for ATP and AMP using pyruvateorthophosphate dikinase 457

Suzuki S, Nishimoto K, Igarashi T, Harada Y, Sakakibara Tand Murakami S

Simultaneous ATP and mitochondrial potential measurements in living cells 461Tourneur Y, Bernengo J-C and Pacheco Y

Cholinesterase inhibitors measured with a chemiluminescence systembased on GZ-11 465

Zomer G, Hamzink MRJ and Bijlsma L

PART 14. ATP-BASED CELL & MICROBIOLOGICAL ASSAYS

In vivo assessment of the effect of diet on time-course of infection inmice using bioluminescent bacterial pathogens 471

Brovko LY, Vandenende C, Chu B, Brooks A and Griffiths MW

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Bioluminescent assay of total bacterial contamination (TBC) in foodsamples and drinking water using Filtravette™ 475

Froundjian VG, Ugarova NN and Trudil DP

Influence of different cyclodextrins on proliferation of HaCaT keratinocytesmeasured by means of bioluminescence and fluorometric assays 479

Hipler C, Hipler U-CH, Eisner P and Wollina U

Influence of melatonin on HaCaT cell proliferation measured by means ofATP bioluminescence and fluorometric assay 483

Hipler U-CH and Eisner P

A comparison of ATP and adenylate kinase as bacterial cell markers:correlation with agar plate counts 487

Squirrell DJ, Murphy MJ, Leslie RL and Green JCD

PART 15. GENE EXPRESSION & REPORTER GENE ASSAYS

Applications of luciferase transfected human cell lines for chemotherapeuticdrug development 493

Andreotti PE, Caceres G, Zankina R, Escano MC and Price V

Non invasive optical imaging of firefly luciferase gene expression inmice using the Berthold Technologies Nightowl LB 981 497

Coll JL Favrot MC and Hennecke M

Application of a luminescence whole-cell biosensor based on a recombinantmouse hepatoma cell line for the detection of dioxin-like chemicals 501

Pasini P, Gentilomi G, Baraldini M, MusianiMand Roda A

Use of bioluminescence for on-line estimation of the production ofrecombinant proteins 505

Trezzani I, Nadri M, Hammouri H, Lieto J, Dorel C, Lejeune P,Dhurjati P, Bellalou J and Longin R

Novel in vivo reporters based on firefly luciferase 509White PJ, Leslie RL Lingard B, Williams JR and Squirrell DJ

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Introduction of GFP-construct into Medakafish using the particlegun method 513

Yamauchi M, Sasanuma M, Tsuji S, Terada M and Ishikawa Y

Index 517